Straightforward Synthesis of Novel 1-(2′-α-O-D-Glucopyranosyl ethyl) 2-Arylbenzimidazoles

Arumugam, Natarajan; Rahim, Aisyah Saad Abdul; Hamid, Shafida Abd; Osman, Hasnah

doi:10.3390/molecules17089887

Cited by 9 publications

(3 citation statements)

References 45 publications

(52 reference statements)

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“…Benzimidazole is a hetero‐bicyclic aromatic compound that comprises two fused rings: benzene and imidazole ring. Benzimidazole derivatives have commonly been synthesized by the reaction of o ‐phenylenediamine derivatives with either carboxylic acids/esters or with aldehydes (Scheme 1) (Arumugam et al, 2012; Kim et al, 2013; Özbey et al, 2002; Rithe et al, 2015). Substitution on N can be achieved through starting with N ‐substituted o ‐phenylenediamine, or via N ‐alkylation of the formed benzimidazole.…”

Section: Chemistrymentioning

confidence: 99%

Benzimidazole‐based protein kinase inhibitors: Current perspectives in targeted cancer therapy

et al. 2022

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Targeted therapy has emerged to be the cornerstone of advanced cancer treatment, allowing for more selectivity and avoiding the common drug toxicity and resistance. Identification of potential targets having vital role in growth and survival of cancer cells got much easier with the aid of the recent advances in high throughput screening approaches. Various protein kinases came into focus as valuable targets in cancer therapy. Meanwhile, benzimidazole‐based scaffolds have gained significant attention as promising protein kinase inhibitors with high potency and varied selectivity. Great diversity of these scaffolds has inspired the medicinal chemists to inspect the effect of structural changes upon inhibitory activity on the molecular level through modeling studies. The present review gathers all the considerable attempts to develop benzimidazole‐based compounds; designed as protein kinase inhibitors with anticancer activity since 2015; that target aurora kinase, CDK, CK2, EGFR, FGFR, and VEGFR‐2; to allow further development and progression regarding benzimidazoles.

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Section: Chemistrymentioning

confidence: 99%

Benzimidazole‐based protein kinase inhibitors: Current perspectives in targeted cancer therapy

et al. 2022

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“…omeprazole, lansoprazole, albendazole and oxfendazole. In recent years, we have been involved in the synthesis of diverse heterocyclic hybrids [23,24,25,26], including biologically-active benzimidazoles [27,28] through cycloaddition/straightforward multistep transformations.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic, X-ray Diffraction and DFT Studies of Novel Benzimidazole Fused-1,4-Oxazepines

et al. 2016

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A series of benzimidazole-tethered oxazepine heterocyclic hybrids has been synthesized in good to excellent yields from an N-alkylated benzimidazole 2-carboxaldehyde, which in turn was accomplished from o-phenylenediamine in three good yielding steps. The calculated molecular structure of compounds 2-methyl-4-(2-((phenylimino)methyl)-1H-benzo-[d]imidazol-1-yl)-butan-2-ol 9 and 10 3,3-dimethyl-N-phenyl-1,2,3,5-tetrahydrobenzo- [4,5]imidazo[2,1-c][1,4]oxazepin-5-amine using the B3LYP/6-31 G(d, p) method were found to agree well with their X-ray structures. The charge distributions at the different atomic sites were computed using the natural bond orbital (NBO) method. The regions of electrophilic and nucleophilic reactivity were shown using a molecular electrostatic potential (MEP) map. In addition, the frontier molecular orbitals of these compounds were discussed at the same level of theory. Nonlinear optical (NLO) properties have also been investigated by computational hyperpolarizability studies, and it was found that Compound 9 is the best candidate for NLO applications.

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“…menthol) propylene carbonate was deployed as solvent. The application of triphenylphosphine and tetrabromomethane in glycosylation processes has been described in the literature [97][98][99][100][101][102][103]. These conditions were applied to glycosylation of fully protected 1-hydroxy carbohydrates.…”

Section: -54 (R'=h R''=h Oh) 56 (R'=ch 2 Oh R''=oh)mentioning

confidence: 99%

Organocatalyzed Glycosylation Reactions of Carbohydrates

Mahrwald¹

2015

SpringerBriefs in Molecular Science

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Several different organocatalyzed glycosylation processes of carbohydrates will be discussed. The results clearly support the concept of the application of unactivated and unprotected carbohydrates in glycosylation processes. By generating hydrogen bridges, which are working during the reaction, the configuration at the anomeric carbon atom can be controlled. Extremely high degrees of stereoselectivities were obtained, depending on the configuration of the carbohydrates deployed.

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Straightforward Synthesis of Novel 1-(2′-α-O-D-Glucopyranosyl ethyl) 2-Arylbenzimidazoles

Cited by 9 publications

References 45 publications

Benzimidazole‐based protein kinase inhibitors: Current perspectives in targeted cancer therapy

Benzimidazole‐based protein kinase inhibitors: Current perspectives in targeted cancer therapy

Synthesis, Spectroscopic, X-ray Diffraction and DFT Studies of Novel Benzimidazole Fused-1,4-Oxazepines

Organocatalyzed Glycosylation Reactions of Carbohydrates

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